


Encounter

by ChibiBox



Category: Pocket Monsters: Sun & Moon | Pokemon Sun & Moon Versions
Genre: Angst, Dysphoria, M/M, Romance, Trans!Reader - Freeform, i mean prepare to be wooed, suave as fuck grimsley
Language: English
Status: In-Progress
Published: 2016-12-29
Updated: 2017-01-02
Packaged: 2018-09-13 06:12:33
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 2,251
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9110071
Author URL: https://archiveofourown.org/users/ChibiBox/pseuds/ChibiBox
Summary: You happen to meet a rather charming albeit edgy looking man in a cafe.----Reader is trans male. Just like my other fic reader is from Sinnoh. Backstory is different however. Reader once again has long hair.





	1. Staring

Your first encounter had been awkward, to say the least.

You'd stopped at a cafe on Ula'Ula, hoping a pinap juice would help cool you off. You hailed from Sinnoh and as such you weren't used to this Alolan heat. Heat that about a year ago would've been much appreciated in your home region.

You never thought you'd miss the cold so much.

You paid the barista and took your juice, sipping it out of a silly straw. Sure, you were in your twenties but who said you had to be mature? You paid for it, you should be allowed to use any straw you wanted, damn it.

You glanced to your left as one of the most...interesting men you'd ever seen sat down beside you.

"A Roserade tea, if you don't mind."

You studied him out of the corner of your eye, giving him a once over as he picked up a menu. Dark circled eyes and sharp black hair streaked with white. This guy screamed edgy. But you couldn't help but think it worked for him. You looked over his odd clothing, a kimono and scarf. Who wore a scarf in that kind of heat?

However, once again, it looked good on him. 

He had slender hands, one of which was flipping a coin across his fingers and back. It was almost mesmerizing. 

You looked back up only to lock eyes with the man, tensing as he smirked at you. He looked vaguely familiar, but you couldn't place where you'd seen him before.

"Studying me, are you?" You jumped slightly, somehow not expecting him to call you on it. But of course he would. Who wouldn't? You'd been incredibly rude to stare at him like that, of course he'd say something.

"You're hard to figure out," you replied, trying to act aloof. You took another sip through your silly straw, lamenting for the first time that such an attractive man had to see you drink from it.

"Oh?" He grinned and leaned forward, leaning on his elbow and propping his chin on his hand. "And what, pray tell, is so hard to figure out?"

You tried to figure out what to say. He in his entirety was hard to figure out! Where could you even start? He took his tea from the barista and sipped it thoughtfully, still looking at you.

"You're wearing a scarf in this heat," you say finally, almost immediately regretting it. That was lame.

Your statement seem to take him by surprise and you watched as the smug grin melted off his face. He clearly hadn't been expecting that and you wondered with shame how much he gets stared at for his appearance.

You relaxed a bit, however, as he started to laugh. A good laugh, rich and deep, and he actually had to clutch his stomach and squeeze his eyes shut. 

You couldn't help but think you wouldn't mind hearing it again.

"My scarf?" He finally quiets down and looks up at you, his cheeks flushed and his teasing demeanor gone for the moment. "Is that all? I just like it, that's all. The heat doesn't bother me much."

You shook your head and sipped your juice. "I don't see how, it's so hot here.." You glanced away, cheeks burning as he studied your face. You weren't used to the attention. 

"Well you're certainly not Alolan," he observed.

"Neither are you." He put his hands up in mock defeat and chuckled. 

"Fair enough. Please excuse my rudeness. My name is Grimsley." He reached out as if to shake your hand and you took it, only to have him raise your hand to his face and give it the gentlest of kisses. You felt your face heat up again as he gave you that teasing smile. "Charmed."

"Uh.." You wondered if you looked as flustered as you felt, then decided you did when his smirk only widened. "(Y/n)..likewise.."

"What a wonderful name." He let go of your hand and finished off his tea, standing and setting some money on the counter. "I do hope we meet again soon, dear (Y/n)." 

With that he turned and started for the door, only to stop short and turn his head towards you just before he left. "There's enough money there for a pinap juice refill, feel free to use it." And with that he left the pokemon center.

You stirred your juice slowly with your silly straw, still slightly embarrassed he'd seen it. Without thinking twice about it you pocketed the money, determined to see him again so you could return it.

You tried to convince yourself that was the only reason. And failed.


	2. Wager

**Summary for the Chapter:**

> You and Grimsley make a pointless bet

No matter how much you asked around for Grimsley it didn't seem like people knew who you were talking about and you wondered if he even told people his name much. Finally you just started describing him, figuring somebody most have noticed him.

It turned out everyone noticed him, because after that people just started directing you to a beach on route 15 where he supposedly spent most of his time. 

"Don't know what the strange fellow does out there and I think I'd prefer to keep it that way." One man said, holding his child slightly behind him as he took in your appearance. You guessed he must be trying to find out your gender so you cleared your throat, causing his eyes to snap back to your face. At least he had the decency to look embarrassed.

"Why do you say that?"

"S'just a strange lookin guy is all. Wouldn't want none of my kids gettin near him, that's for sure." You scowled at that. Sure Grimsley was a bit eccentric but he'd been nice to you when you met him.

"Maybe you shouldn't judge people by their appearances." You turned with that and started for route 15, not wanting to be part of that conversation any longer.

What were you supposed to say to him? Should you even say anything? You were only going to give his money back, right?

You groaned internally as a little voice in your mind told you that, no, that wasn't the only reason and that you found him very interesting.

And dare you think again, attractive.

There was just something about him. Something so elegant yet spontaneous, like he could do anything, something wild and unexpected at any given moment but would do it with grace.

Like a Liepard, you thought.

You came upon the small beach and, lo and behold, there he was, just staring out at the water. You wondered if this is really what he does all day. Did he have a home? Did he live on the beach, perhaps?

You took a deep breath and stepped onto the sand, making your way towards him slowly as if he'd startle at any moment.

It was you who startled, however, when he turned his head and gave you that smile. Suddenly your throat felt very dry.

"Well hello. I didn't expect to see you so soon, dear (Y/n). Did you perhaps have some business to discuss?"

You nodded and pulled the cash out of your pocket. "I came to give this back.."

He walked over and took it from you gently. "You could've kept it if you'd wanted."

"I don't like to take advantage." He raised an eyebrow at that, as if you doing the right thing was baffling to him.

"You wouldn't have been but I must say I'm glad you gave it back if it made you feel that way." He smiled that teasing smile and pocketed the money. "I suppose I can always buy you a drink with it later."

It was your turn to raise your eyebrow, and you had to fight to keep a smile off your face. "Later?"

"Well I don't mean to assume but I would love to see you again." You blushed a little at that. Someone as graceful and poised as him wanted to see you again? You were honestly flattered, not thinking yourself as a very interesting person.

"Why don't we make a little wager?" He suddenly stated, snapping you out of your thoughts.

"A wager?" He smiled again and your heart did a backflip. You watched as he pulled the same gold coin from earlier out of his pocket.

"We'll flip a coin. If I win, I take you to dinner." Your cheeks were feeling hotter by the minute.

"And if I win?"

"Then you can have whatever your little heart desires." He flipped the coin over his fingers and back, his grin widening. "So. Heads or tails?"

Surely it wouldn't be as easy as picking a side with this guy. He had to have something up his sleeve. You looked at his face, a face grinning as if he knew something you didn't and you took a chance.

"Neither." You boldly proclaimed.

He stayed silent for a few moments and you began to feel embarrassed about your decision when he gave a soft laugh. 

"Astonishing." You blinked in surprise as a Skarmory landed behind him. "I had indeed intended to have Skarmory snatch the coin out of the air before it could land." 

Even in the short amount of time you'd known this man, it didn't strike you as something he wouldn't do. "So...I win?"

"You win."

You thought about it for a moment. What did you want from this man? You thought about the way he kissed your hand and your face grew hot once more. You knew what you wanted.

"Dinner, then." He raised his eyebrows at you.

"So I could've just asked, hm?"

"Well, I..." was all you were able to respond with. You didn't even have an excuse, you were just very attracted to him.

He smiled and started to exit the beach. "Meet me here Friday at seven. Until then, dear (Y/n)."

You had a date.

What the fuck were you going to wear?

**Notes for the Chapter:**

> I guess I just have a thing for edgy boys tbh


	3. Preparation

**Summary for the Chapter:**

> You buy some clothes for your date

You decided to go clothes shopping before you went home, thinking it was best to get it out of the way now so you weren't unprepared later. You started for Konikoni City, knowing if anywhere had what you were looking for, it would be there.

Upon arrival you immediately headed toward the multiregional section and spotted what you were looking for. Kimonos and other similar outfits. There weren't many but what few they had were gorgeous.

You'd never worn a kimono before and frankly you had no idea what to look for in terms of size but the lady at the counter was more than happy to help you out. You tried them all on before settling on an outfit you liked: a deep teal knee length yukata with a winding red flower pattern, thigh high socks, and simple dark red flats. The flats pinched your toes a bit but you wouldn't wear them except for Friday.

Or, you thought hopefully. Maybe a few Fridays if I'm lucky.

Perhaps you were catering to Grimsley's taste but you had to admit the yukata was quite comfortable. You redressed and paid for your items, exiting the store to head for your motel room.

You entered and carefully put your new outfit away, not wanting to damage it, and then crashed onto your bed and put your face into your pillow.

You weren't sure if it was nervousness or excitement or both but you found it hard to sleep, having jitters the rest of the night.

\---

Finally Friday came and you made your way to route 15, stopping occasionally to adjust your painful flats. You really needed to break these in, it was torture. You pulled your hair up into a quick bun, hoping it would look like you at least spent a little time styling it, and stepped onto the beach.

Grimsley wasn't there yet but you weren't bothered, knowing you'd gotten there early, and stood at the shoreline, watching the waves crash gently onto the beach. You weren't very fond of the ocean, having been landlocked most of your life in Sinnoh, but it had it's little charms. The sea breeze was nice, as was the warm sand between your toes, but as a whole the ocean frightened you a little. A vast stretch of water, with land miles and miles between? You'd rather stay on land, thank you very much.

With that in mind you wondered why you moved to a place that was literally mostly ocean.

"Ah, you're here. I hope I didn't keep you waiting long."

You smiled a bit and turned to Grimsley, tugging self consciously at the bottom of your yukata. "I just arrived myself, don't worry."

"Ah good, I would hate to disappoint." He stopped in front of you and smiled teasingly, giving a gentle tug at your sleeve. "Is this for me?"

You felt your face heat up, somehow forgetting that he liked to embarrass you. What scared you just a bit was you thought you liked it. "Well...it's not fair that you're always dressed up, I thought I'd try to look nice."

"Well, I must say you've done a great job. You look lovely." With that he took your hand and kissed it again, very gently, and gave you that charming smirk. You were going to melt if he kept this up.

He offered you his arm. "Shall we be going?"

You took it without hesitation, nervous but excited beyond comprehension. You just hoped this went well.

**Notes for the Chapter:**

> Not even gonna lie tho yukatas look comfy af
> 
> I kno this chapter's rly short but I gotta set up for the next one

**Author's Note:**

> Grimsley seemed fun to write so I thought I'd give this a shot.
> 
> Please tell me what you think!


End file.
